[6-tert-butoxycarbonylamino-4-{[1-(2-nitrobenzenesulfonyl)piperidin-4-yl]methyl}pyridine-2-yl]methanol

Base Information

• Chemical Name: [6-tert-butoxycarbonylamino-4-{[1-(2-nitrobenzenesulfonyl)piperidin-4-yl]methyl}pyridine-2-yl]methanol
• CAS No.: 1323264-39-6
• Molecular Formula: C₂₃H₃₀N₄O₇S
• Molecular Weight: 506.58

Synonyms:[6-tert-butoxycarbonylamino-4-{[1-(2-nitrobenzenesulfonyl)piperidin-4-yl]methyl}pyridine-2-yl]methanol

Chemical Property of [6-tert-butoxycarbonylamino-4-{[1-(2-nitrobenzenesulfonyl)piperidin-4-yl]methyl}pyridine-2-yl]methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of [6-tert-butoxycarbonylamino-4-{[1-(2-nitrobenzenesulfonyl)piperidin-4-yl]methyl}pyridine-2-yl]methanol

There total 9 articles about [6-tert-butoxycarbonylamino-4-{[1-(2-nitrobenzenesulfonyl)piperidin-4-yl]methyl}pyridine-2-yl]methanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

methyl 6-tert-butoxycarbonylamino-4-{[1-(2-nitrobenzenesulfonyl)piperidin-4-yl]methyl}pyridine-2-carboxylate (1323264-37-4) → [6-tert-butoxycarbonylamino-4-{[1-(2-nitrobenzenesulfonyl)piperidin-4-yl]methyl}pyridine-2-yl]methanol (1323264-39-6)

Guidance literature:

With sodium tetrahydroborate; calcium chloride; In ethanol; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1135/cccc2011017

Reference yield:

chelidamic acid (138-60-3) → [6-tert-butoxycarbonylamino-4-{[1-(2-nitrobenzenesulfonyl)piperidin-4-yl]methyl}pyridine-2-yl]methanol (1323264-39-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: phosphorus pentabromide / chloroform / 3 h / 90 °C / Inert atmosphere

2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / Inert atmosphere; Reflux

2.2: 0.17 h / 20 °C / Inert atmosphere

3.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

4.1: dmap; triethylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere

5.1: potassium hydroxide / methanol; dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

6.1: diphenyl phosphoryl azide; triethylamine / toluene / 16 h / 100 °C / Inert atmosphere

7.1: sodium tetrahydroborate; calcium chloride / ethanol / 2 h / 0 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; diphenyl phosphoryl azide; phosphorus pentabromide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; trifluoroacetic acid; calcium chloride; potassium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; toluene; 6.1: Curtius rearrangement;

DOI:10.1135/cccc2011017

Reference yield:

dimethyl 4-[(1-tert-butoxycarbonylpiperidin-4-yl)methyl]pyridine-2,6-dicarboxylate (1323264-30-7) → [6-tert-butoxycarbonylamino-4-{[1-(2-nitrobenzenesulfonyl)piperidin-4-yl]methyl}pyridine-2-yl]methanol (1323264-39-6)

Guidance literature:

Multi-step reaction with 5 steps

1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

2: dmap; triethylamine / dichloromethane / 16 h / 20 °C / Inert atmosphere

3: potassium hydroxide / methanol; dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

4: diphenyl phosphoryl azide; triethylamine / toluene / 16 h / 100 °C / Inert atmosphere

5: sodium tetrahydroborate; calcium chloride / ethanol / 2 h / 0 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; diphenyl phosphoryl azide; triethylamine; trifluoroacetic acid; calcium chloride; potassium hydroxide; In methanol; ethanol; dichloromethane; toluene; 4: Curtius rearrangement;

DOI:10.1135/cccc2011017

upstream raw materials:

dimethyl 4-[(1-tert-butoxycarbonylpiperidin-4-yl)methyl]pyridine-2,6-dicarboxylate

C₁₅H₂₀N₂O₄

dimethyl 4-{[1-(2-nitrobenzenesulfonyl)piperidin-4-yl]methyl}pyridine-2,6-dicarboxylate

6-methoxycarbonyl-4-{[1-(2-nitrobenzenesulfonyl)piperidin-4-yl]methyl}pyridine-2-carboxylic acid

Downstream raw materials:

N-(1-[{6-amino-4-[(1-propylpiperidin-4-yl)methyl]pyridin-2-yl}methyl]piperidin-4-yl)-2-cyclopentyl-2-hydroxy-2-phenylacetamide

4-tert-butoxycarbonylamino-1-[6-tert-butoxycarbonylamino-4-([{[1-(2-nitrobenzenesulfonyl)piperidin-4-yl]methyl}pyridin-2-yl]methyl)]piperidine

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